Zhang Zhikun, Hu Xile
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Poly-technique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne, 1015, Switzerland.
Angew Chem Int Ed Engl. 2021 Oct 11;60(42):22833-22838. doi: 10.1002/anie.202107570. Epub 2021 Sep 7.
Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst is essential to ensure two distinct pathways for the forward and reverse reactions. These reactions convert a large number of racemic aryl alkyl alcohols into their enantiomerically enriched forms in good yields and enantioselectivities.
外消旋手性化合物的去消旋化是不对称合成中一种有吸引力的方法，但其发展受到能量和动力学挑战的阻碍。在此，我们描述了一种用于仲苄醇的催化去消旋化方法，仲苄醇是许多行业重要的合成中间体和最终产品。该方法仅由可见光驱动，基于顺序光化学脱氢，随后进行对映选择性热氢化。非均相脱氢光催化剂和手性分子氢化催化剂的组合对于确保正向和反向反应的两条不同途径至关重要。这些反应能以良好的产率和对映选择性将大量外消旋芳基烷基醇转化为其对映体富集形式。
